8-HYDROXYLATED DERIVATIVES OF DIAZABICYCLO[4.3.0]NONANES, 2,5-DIOXODIAZABICYCLO[4.3.0]NONANES AND SOME RELATED ESTERS

Pharmacological considerations prompted the authors to synthesize a series of 8-hydroxylated optically active derivatives of diazabicyclo[4.3.0]nonanes and of their 2,5-dioxo analogs from trans-4-hydroxy-L-proline. Esterification with appropriate anhydrides led to the corresponding esters with 6S,8R configuration. Inversion of configuration at C-8 was performed using Mitsunobu method and led to the diastereoisomeric series of 6S,8S esters. A tentative pharmacological evaluation was carried out in the area of sedative and spasmolytic activities.